Water → 4-[[4-(2,4,6-Trimethylphenoxy)-2-pyrimidinyl]amino]benzonitrile

HRID 1294425Notes

Reaction equation

HRID 1294425 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([CH3:11])[C:5]=1[OH:12].Cl[C:14]1[CH:19]=[CH:18][N:17]=[C:16]([NH:20][C:21]2[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=2)[N:15]=1.O>O1CCOCC1>[CH3:3][C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([CH3:11])[C:5]=1[O:12][C:18]1[CH:19]=[CH:14][N:15]=[C:16]([NH:20][C:21]2[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=2)[N:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 106982,4,6-TrimethylphenolHCID 24758Sodium hydrideHCID 111955954-((4-Chloropyrimidin-2-yl)amino)benzonitrile

Product 1

HCID 4887674-[[4-(2,4,6-Trimethylphenoxy)-2-pyrimidinyl]amino]benzonitrileYield 89.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a suspension of NaH (0.006 mol) in 1,4-dioxane (30 ml), 2,4,6-trimethyl-phenol (0.006 mol) was added. The mixture was stirred for 15 minutes at room temperature, and a clear solution formed. 4-[(4-chloro-2-pyrimidinyl)amino]benzonitrile (0.004 mol) was added, and the reaction mixture was heated to reflux under Argon for 15 hours. The reaction mixture was allowed to cool to room temperature, 0.5 ml of water was added, followed by 4 g of silica gel, and the solvent was evaporated. The residue was purified by flash column chromatography over silica gel (eluent gradient: CH2Cl2:CH3OH 100:0:0 to 97:3). The pure fractions were collected and the solvent was evaporated, yielding 1.18 g (89.4%) of 4-[[4-(2,4,6-trimethylphenoxy)-2-pyrimidinyl]amino]benzonitrile (comp. 20).

Workup

  1. additionwas added
  2. customa clear solution formed
  3. temperaturethe reaction mixture was heated
  4. temperatureto reflux under Argon for 15 hours
  5. temperatureto cool to room temperature
  6. customthe solvent was evaporated
  7. customThe residue was purified by flash column chromatography over silica gel (eluent gradient: CH2Cl2:CH3OH 100:0:0 to 97:3)
  8. customThe pure fractions were collected
  9. customthe solvent was evaporated

Sources & evidence

ORD record
ord-4e7220904d584d85929dd2954c154e1a
Source dataset
uspto-grants-2007_07
Patent number
US07241458B1

Reaction notes

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